Flavored tobacco product

ABSTRACT

Addition of mesityl oxide condensation products to tobacco to enhance the flavor and/or aroma thereof. The identifiable compounds in the condensation which have been found to be effective are 2-isopropenyl-1-3-5, 5-trimethyl-2cyclohexen-1- one, 1(cis-2 ketopropylidenyl) -3, 5,5 -trimethyl 2-cyclohexene, 1-(trans-2-ketopropyl-lidenyl)-3, 5,5-trimethyl-2cylohexene, 5, 5-dimethyl -3-isobutenyl-2- cyclohexen-1- one and 2-acetyl-1, 3-didimethyl -4-isopropylcyclopentadiene and mixtures thereof.

United States Patent 11 1 Roberts Dec. 25, 1973 [54] FLAVORED TOBACCO PRODUCT Prima ExaminerMelvin D. Rein 1) 1d R rts w t 1 [75] Inventor g L obe ms on Sa em Attorney-Albert H. Pendleton et al.

[73] Assignee: R. J. Reynolds Tobacco Company, B TRACT Winston-Salem, NC. [57] A Addition of mesityl oxide condensation products to Flled: P 1972 tobacco to enhance the flavor and/or aroma thereof.

[21] Appl. No.: 289,856 The identifiable compounds in the condensation which have been found to be effective are 2-isopropeny1 1-3, 5, 5-trimethy1-2- cyclohexen-l- Cll. l3llk7i4lb3ilsllgj 1 (cisa p py y mmethyl [58] Field "131/17 144 Qwwlohexene, 1 (trans 2 ket0propyl 1i yn 5,5 trimethyl 2 cylohexene 5 dimethyl [56] References Cited -3-isobutenyl-2- cyclohexen-lone and 2-acetyl-1-, 3-di dimethyl -4-isopropylcyclopentadiene and UNITED STATES PATENTS mixtures thereof 3,217,718 11/1965 Roberts 131/17 R 3,380,456 4/1968 Roberts et al. 131 144 x 10 ClalmS, N0 Drawmgs FLAVORED TOBACCO PRODUCT on. on.

This invention relates to tobacco and tobacco products and has for an object the provision of compositions and processes for improving the flavor and/or aroma of 5 tobacco and tobacco smoke.

It is well known in the tobacco art that the flavor and aroma of tobacco products and the smoke from the tobacco are very important considerations insofar as the ultimate consumer is concerned. Considerable efforts Compound IV l-(trans-Z-Ketopropylidenyl)-3,5,5- trimethyl-Z-cyclohexene are exerted by the manufacturers of tobacco products to provide a product that will be acceptable to the consumer, particularly as regards flavor and aroma characteristics. It has been the common practice in the tobacco industry to prepare blends of domestic and ori- CH:

ental tobaccos in order to provide smoking tobacco which has a pleasing flavor and aroma before and during smoking. However, such a procedure is costly and may at times become prohibitive in the event that certain types of tobacco may be in short supply. Accordingly, it is a further object of this invention to provide a class of additive materials which when applied to the tobacco products improve and enhance the flavor and aroma of these products and the smoke emitted therefrom thereby increasing or enhancing the pleasure and i other values that may be derived by the consumer from 4 the use of these products.

A further object of this invention is the provision of processes for enhancing or otherwise improving the flavor, aroma and other qualities of certain domestic, oriental, reconstituted or synthetic tobaccos which may be deficient in said flavor or aroma or other qualities.

A still further object of this invention is the provision of smoking products, such as cigarettes, cigars or pipe tobacco, and a process for forming same whereby the flavor and aroma before and during smoking are improved or enhanced.

Further and additional objects will appear from the following description and the appended claims.

In accordance with this invention, the flavor and/or 4 aroma of tobacco or tobacco products is improved by adding thereto a small amount of a compound or mixture of compounds resulting from a base catalyzed conthe refluxlrlg bemgmnducted for a penod of to 24 densation of mesityl oxide hours. variousbaslc catalysts can be employedfor the Autocondensation of mesityl oxide in the presence of futoconflensaufm such for efamplegmagneslumPx' a base yields a mixture of condensation products in- 'f calcufm oxlde"sodmm hydroxlde, eluding; Compound I lsophol-one potassium hydroxide, sodium ethoxide, sodium pentoxide, sodamide, basic ion exchange resins and the like.

Compound V cyclohexen-l-one 5 ,5-Dimethyl-3-isobutenyl-2- Compound Vl 2-Acetyl-l,3-dimethyl-4-isopropylcyclopentadiene H CH3 CHg-C CH3 ClCHa 0 The above compounds can be synthesized simply by refluxing mesityl oxide in the presence of a base for a period sufficient to effect autocondensation; generally CH8 CH: The products of the autocondensation can be separated by suitable procedures such as fractional distillation, chromatography, etc. Also, the entire product mixture resulting from the base catalyzed condensation of mesi- O -CH:

Compound 11 cyclohexen- 1 -one 2-lsopropenyl-3,5,5-trimethyl-2- CH: CH:

tyl oxide can be used to flavor tobacco or tobacco products.

The above compounds are known to the literature and, for example, have been disclosed as autocondensation products of mesityl oxide in the presence of magnesium oxide by A. Roger, J. Godfroid and J. Wiemann in Bull. Soc. Chim. Fr. 1067, (8), 3030-3037. Similarly, an investigation into the nature of the products obtained from the autocondensation of mesityl oxide under basic conditions has been reported by B. Furth and J. Wiemann in Bull. Soc. Chim. Fr. 1965 (6), 1819-1831.

Illustrative of the preparation of compounds which following:

A mixture consisting of 98 grams of mesityl oxide,

hydroxide dissolved in 20 milliliters of ethanol was heated at reflux temperatures for 2 hours. The mixture was cooled and poured into 500 milliliters of water containing 34 grams of acetic acid. The organic phase was separated, dried and subjected to fractional distillation using an 18-inch spinning band column. The fraction (4.09 grams) boiling at 75-80 C./0.2 millimeter of mercury was identified as 2-isopropenyl-3,5,5- trimethyl-Lcyclohexen-l-one (Compound ll). The infrared spectrum displayed characteristic bands at 1668, 1608, 1579, 1308, 1284, i249 and 898 cm".

In practice of this invention an above compound or mixtures thereof is added to tobacco or applied to a tobacco product or its component parts in amounts of from about 0.00001 to about 0.1 percent by weight of .the tobacco or tobacco product. Preferably, the amount of additive is between about 0.0001 and 0.001 percent by weight. However, the amount used will depend upon the amount of flavor and/or aroma desired and the particular compound or mixtures thereof that is used.

The additives can be incorporated at any step in treatment of the tobacco but are preferably added after aging, curing and shredding and before the tobacco is formed into cigarettes or other products. Likewise, it will be apparent that only a portion of the tobacco need be treated and the thus treated tobacco can be blended with other tobaccos before the cigarettes or other to bacco products are formed. In such case the treated tobacco may have the additive in excess of the amounts above indicated so that when blended with other tobaccos the final product will contain a percentage of additive within the indicated range.

The tobacco additives of the invention when incorporated into tobacco products improve the flavor and/or aroma of the product. However, it is to be appreciated that definition or characterization of flavor or aroma in the tobacco art is almost purely subjective and different smokers may define the same flavor or effect quite differently. With this in mind, characterization of the effect of representative tobacco additives of this invention in cigarettes has been made as follows:

Additive Corn pou nd 1! smoothing, sweet adds body In accordance with one specific embodiment of this invention, an aged flue-cured and shredded tobacco is sprayed with a 1 percent ethyl alcohol solution of 2- isopropenyl-3,5,5-trimethyl-2-cyclohexen-l-one in an amount toprovide a tobacco containing 0.001 percent by weight of the additive on a dry basis. Thereafter the alcohol is removed by evaporation and the tobacco is manufactured into cigarettes by the usual techniques. The cigarette when prepared as indicated has an improved character when smoked.

The additives falling within the scope of this invention may be applied to the tobacco by spraying, dipping or otherwise, utilizing suitable suspensions or solutions of the additives. Thus, water or volatile organic solvents, such as alcohol, ether, acetone, volatile hydrocarbons and the like, may be used as the carrying medium for the additives while being applied to the tobacco. Also, other flavorand aroma-producing additives, such as those disclosed in US. Pat. Nos. 2,766,145, 2,905,575, 2,905,576, 2,978,365 and 3,041,211 may be incorporated into the tobacco with the additives of this invention.

While this invention is principally useful in the manufacture of cigarette tobacco, it is also suitable for use in connection with the manufacture of pipe tobacco, cigars or other tobacco products. Furthermore, the additives can be added to certain tobacco substitutes of natural or synthetic origin and by the term tobacco" as used throughout this specification is meant any composition intended for use by smoking or otherwise, whether composed of tobacco plant parts or substitute materials or both.

Also, the invention has been particularly described with reference to the addition of the additives directly to tobacco. However, it will be apparent that the addi tives can be applied to the paper of the cigarette or to the wrapper of a cigar. Also, they can be incorporated into the filter tip, the packaging material or the seam paste employed for gluing the cigarette paper. Thus, a tobacco product is provided which includes the specifled additives and tobacco although in every instance the compound need not be admixed with the tobacco as above specifically described.

Those modifications and equivalents which fall within the spirit of the invention are to be considered a part thereof.

What is claimedisi l. A tobacco product having added thereto a small amount sufficient to alter the flavor or aroma of the tobacco product of a compound selected from the group consisting of 2-isopropenyl-3,5,S-trimethyl-Z- cyclohexen-l-one, l-(cis-Z-ketopropylidenyl)-3,5,5- trimethyl-Z-cyclohexene, l-(trans-Z- ketopropylideny])-3,5,5-trimethyl-2-cyclohexene, 5,5- dimethyl-3-isobutenyl-2-cyclohexen-l-one and 2- acetyll ,3-dimethyl-4-isopropylcyclopentadiene and mixtures thereof.

2. The product recited in claim 1 wherein the amount of said compound added to the product is between about 0.00001 and about 0.1 percent by weight of the product.

3. A product according to claim 1 wherein the compound added is 2-isopropenyl-3,5,S-trimethyl-Z- cyclohexen-l-one.

4. A product according to claim 1 wherein the compound added is l-(cis 2-ketopropylidenyl)-3,5,5- trimethyl-2-cyclohexene.

5. A product according to claim 1 wherein the compound added is 1-(trans-2-ketopropylidenyl)-3,5,5- trimethyl-Z-cyclohexene.

6. A product according to claim 1 wherein the compound added is 5 ,5-dimethyl-3-isobutenyl-2- cyclohexen- 1 -one.

7. A product according to claim 1 wherein the compound added is 2-acetyl-1,3-dimethyl-4-isopropylcyclopentadiene.

8. A process for improving the flavor of tobacco which comprises adding thereto a small amount sufficient to alter the flavor or aroma of the tobacco of a compound selected from the group consisting of 2- isopropeny1-3 ,5 ,5-trimethyl-2-cyclohexen- 1 -on,e, l- (cis-2-ketopropylidenyl )-3 ,5 ,5-trimethyl-2- trimethyl-Z-cyclohexene, 1-(trans-2ketopropylidenyl)- 3,5,5-trimethyl-2-cyclohexene, 5,5-dimethyl-3- isobutenyl-Z-cyclohexen- 1 -one and 2-acetyl-l ,3- dimethyl-4-isopropylcyclo-pentadiene.

10. The process of claim 9 wherein a compound recited therein is added to the tobacco in an amount between about 0.00001 and about 0.1 percent by weight of the tobacco.

UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3 780, 743 Dated December 25 2 2g Invent Donald L. Roberts It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:

On the first page of the patent, lines 5-10 of the Abstract should read as follows: 2-isopropenyl 3,5,S-trimethyl- Z-cyclohexen-l-one, 1- 9 1'. s-'2- ketopropylidenyl)3,5;-5- trimethyl-Z-cyclohexene, l- (E -Z-ketQ rQpylidenyIM- 3,5,5- trimethy l-2-cyclohexene, 5,5-dimethYl-3- isobutenyl-Z-cyclohexen-l-one and 2-acet-yl-l,3-

dimethyl-4-isopropylcyclopentadiene and Column 2, line 60, "1067 should be 19'67 Signed and sealed this 7th day of May 1971;.

(SEAL) Attestz- IBDI-IAED I-LI-LETCIEIR, JR. C; MARSHALL DAMN Attesting Officer Commissioner of Patents FORM PO-1050l10-69) uscoMM-Dc 603764569 nu. will!!! P I IIITINGPFHCI 1 I) o-qu-n; 

2. The product recited in claim 1 wherein the amount of said compound added to the product is between about 0.00001 and about 0.1 percent by weight of the product.
 3. A product according to claim 1 wherein the compound added is 2-isopropenyl-3,5,5-trimethyl-2-cyclohexen-1-one.
 4. A product according to claim 1 wherein the compound added is 1-(cis-2-ketopropylidenyl)-3,5,5-trimethyl-2-cyclohexene.
 5. A product according to claim 1 wherein the compound added is 1-(trans-2-ketopropylidenyl)-3,5,5-trimethyl-2-cyclohexene.
 6. A product according to claim 1 wherein the compound added is 5,5-dimethyl-3-isobutenyl-2-cyclohexen-1-one.
 7. A product according to claim 1 wherein the compound added is 2-acetyl-1,3-dimethyl-4-isopropylcyclopentadiene.
 8. A process for improving the flavor of tobacco which cOmprises adding thereto a small amount sufficient to alter the flavor or aroma of the tobacco of a compound selected from the group consisting of 2-isopropenyl-3,5,5-trimethyl-2-cyclohexen-1-one, 1-(cis-2-ketopropylidenyl)-3,5,5-trimethyl-2-cyclohexene, 1-(trans-2-ketopropylidenyl)-3,5,5-trimethyl-2-cyclohexene, 5,5-dimethyl-3-isobutenyl-2-cyclohexen-1-one and 2-acetyl-1,3-dimethyl-4-isopropylcyclopentadiene.
 9. A process for improving the flavor of a tobacco product which comprises adding thereto a small amount sufficient to alter the flavor or aroma of the tobacco product of a compound selected from the group consisting of 2-isopropenyl-3,5,5-trimethyl-2-cyclohexen-1-one, 1-(cis-2-ketopropylidenyl)-3,5,5-trimethyl-2-cyclohexene, 1-(trans-2ketopropylidenyl)-3,5,5-trimethyl-2-cyclohexene, 5,5-dimethyl-3-isobutenyl-2-cyclohexen-1-one and 2-acetyl-1,3-dimethyl-4-isopropylcyclo-pentadiene.
 10. The process of claim 9 wherein a compound recited therein is added to the tobacco in an amount between about 0.00001 and about 0.1 percent by weight of the tobacco. 